(Pyridin-4-yl)boronic acid → N-(6-(6-Chloro-5-(methylsulfonamido)pyridin-3-yl)-3-(pyridin-4-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide

Participants

Reaction Steps

Following the procedure described for N-(6-(6-chloro-5-(methylsulfonamido)pyridin-3-yl)-3-(3-fluorophenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide (TFA salt) (Example 22), N-(6-(6-chloro-5-(methylsulfonamido)pyridin-3-yl)-3-iodoimidazo[1,2-b]pyridazin-2-yl)acetamide (0.250 g, 0.493 mmol) (Example 21) was reacted with pyridine-4-boronic acid (0.0606 g, 0.493 mmol, Boron Molecular) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II)dichloromethane adduct (0.040 g, 0.049 mmol, Strem Chemical, Inc., Newburyport, Mass.) for 6 h at 90° C. to afford the title compound as a yellow solid (0.080 g, 28%). MS (ESI, positive ion) m/z: 458 (M−TFA+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.12 (s, 3H), 3.24 (s, 3H), 8.17 (d, J=9.6 Hz, 1H), 8.27 (d, J=6.1 Hz, 2H), 8.42 (d, J=9.4 Hz, 1H), 8.61 (d, J=2.0 Hz, 1H), 8.79 (d, J=6.1 Hz, 2H), 9.01 (d, J=2.0 Hz, 1H), 9.98 (br s, 1H), 10.76 (s, 1H).

Provenance & Evidence